2304-85-0

Usage

Uses

Used in Organic Synthesis:
Pyrene-1,8-dione is utilized as a reagent in organic synthesis, serving as a key component in the creation of various organic compounds. Its unique properties make it a valuable asset in the synthesis process.
Used in Materials Science and Technology:
In the field of materials science and technology, pyrene-1,8-dione is employed for its potential to contribute to the development of new materials with enhanced properties.
Used in the Development of Organic Electronic and Optoelectronic Devices:
Pyrene-1,8-dione is being studied for its potential use in the development of new organic electronic and optoelectronic devices, where its strong fluorescence and other properties could be harnessed to improve device performance.
Used in Photodynamic Therapy:
Pyrene-1,8-dione has been investigated for its photodynamic therapy properties, indicating its potential use in the treatment of certain medical conditions, such as cancer. This application leverages its ability to interact with light to promote therapeutic effects.
Overall, pyrene-1,8-dione is a versatile compound with a wide range of potential applications across different scientific and technological fields, making it a compound of significant interest for further research and development.

InChI:InChI=1/C16H8O2/c17-13-7-3-9-1-2-10-4-8-14(18)12-6-5-11(13)15(9)16(10)12/h1-8H

Upstream product

• 129-00-0 pyrene 
• 5315-79-7 1-hydroxypyrene 
• 696-33-3 iodoxybenzene 

Downstream Products

• 23353-92-6 5H-cyclopentaphenalen-5-one 
• 187-78-0 Pyracyclen 
• 78078-85-0 1,8-dihydroxypyrene 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 1253622-52-4 C₇₂H₄₂ 

Relevant academic research and scientific papers

Pyrenediones as versatile photocatalysts for oxygenation reactions with: In situ generation of hydrogen peroxide under visible light

Pyrenediones (PYDs) are efficient photocatalysts for three oxygenation reactions: Epoxidation of electron deficient olefins, oxidative hydroxylation of organoborons, and oxidation of sulfides via in situ generation of H2O2 under visible light irradiation, using oxygen as a terminal oxidant and IPA as a solvent and a hydrogen donor.

Aerobic C-H Functionalization Using Pyrenedione as the Photocatalyst

We disclose a visible-light-promoted aerobic alkylation of activated C(sp 3)-H bonds using pyrenedione (PYD) as the photocatalyst. Direct C-H bond alkylation of tetrahydrofuran with alkylidenemalononitriles is accomplished in over 90% yield in the presence of 5 mol% of PYD and 18 W blue LED light under ambient conditions. The substrate scope is extended to ethers, thioethers, and allylic C-H bonds in reactions with various electrophilic Michael acceptors. The catalytic turnover process is facilitated by oxygen. Our work represents the first example of using PYD as a photocatalyst to promote C(sp 3)-H alkylation, revealing the unique character of PYD as a novel organophotocatalyst.

Sterically driven metal-free oxidation of 2,7-di-tert-butylpyrene

We disclose an unprecedented single-step metal-free green oxidation of 2,7-di-tert-butylpyrene selectively into either the corresponding 4,5-dione or 4,5,9,10-tetraone, two key building blocks used for organic optoelectronic applications using hypervalent

A comparison of optical, electrochemical and self-assembling properties of two structural isomers based on 1,6- and 1,8-pyrenedione chromophores

Two isomeric donor-acceptor-donor (DAD) pyrene chromophores were synthesized and their optical, electrochemical and solid-state properties were investigated. Both chromophores showed similar light absorption profiles that spanned the visible region from 3

Copper(i)-based oxidation of polycyclic aromatic hydrocarbons and product elucidation using vacuum ultraviolet spectroscopy and theoretical spectral calculations

Copper(i) complexes supported by fluorinated 1,3,5-triazapentadienyl ligands have been used as catalysts for the oxidation of anthracene, naphthalene, and pyrene to the corresponding quinones, using H2O2 as an oxidant under mild conditions without an acid co-catalyst. Gas chromatography-vacuum ultraviolet spectroscopy (GC-VUV) combined with time-dependent density functional theory theoretical computations of absorption spectra was demonstrated as a new and useful tool-set for unknown determination in complex reaction mixtures, especially when standards are not available for spectral comparisons and product mixtures involve closely related isomers. The anthracene has been converted to 9,10-anthraquinone in quantitative yield using this copper catalyzed process. The oxidation of naphthalene afforded 1,4-naphthoquinone as the major product, and 1-naphthol and 2-naphthol as minor products. The pyrene oxidation resulted in 4,5-, 1,6-, and 1,8-pyrenequinones, among other products. The X-ray crystal structure of [N{(CF3)C(C6F5)N}2]CuNCCH3 is also reported.

Synthesis of o-Carboxyarylacrylic Acids by Room Temperature Oxidative Cleavage of Hydroxynaphthalenes and Higher Aromatics with Oxone

A simple procedure for the synthesis of a variety of o-carboxyarylacrylic acids has been developed with Oxone (2KHSO5·KHSO4·K2SO4); the oxidation reaction involves the stirring of methoxy/hydroxy-substituted naphthalenes, phenanthrenes, anthracenes, etc. with Oxone in an acetonitrile-water mixture (1:1, v/v) at rt. Mechanistically, the reaction proceeds via initial oxidation of naphthalene to o-quinone, which undergoes cleavage to the corresponding o-carboxyarylacrylic acid. The higher aromatics are found to yield carboxymethyl lactones derived from the initially formed o-carboxyarylacrylic acids.

Biomimetic oxidation of pyrene and related aromatic hydrocarbons. Unexpected electron accepting abilities of pyrenequinones

We present a mild catalytic method to oxidize PAHs and, in particular, pyrene. The pyrenediones are much better electron acceptors than benzoquinone in the gas phase and present similar accepting abilities in solution.

Photodegradation mechanisms of 1-nitropyrene, an environmental pollutant: The effect of organic solvents, water, oxygen, phenols, and polycyclic aromatics on the destruction and product yields

This work describes studies of the photodegradation mechanism of 1-nitropyrene (1-NO2Py) in a chemical model system consisting of an organic solvent and known constituents of an aerosol particle. Photoproducts such as 1-hydroxypyrene (1-OHPy),

Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

The hypervalent iodine reagents o-iodoxybenzoic acid (IBX) and bis(trifluoro-acetoxy)iodobenzene (BTI) are shown to be general reagents for regio-controlled oxidation of polycyclic aromatic phenols (PAPs) to specific isomers (ortho, para, or remote) of polycyclic aromatic quinones (PAQs). The oxidations of a series of PAPs with IBX take place under mild conditions to furnish the corresponding ortho-PAQs. In contrast, oxidations of the same series of PAPs with BTI exhibit variable regiospecificity, affording para-PAQs where structurally feasible and ortho-PAQs or remote PAQ isomers in other cases. The structures of the specific PAQ isomers formed are predictable on the basis of the inherent regioselectivities of the hypervalent iodine reagents in combination with the structural requirements of the phenol precursors. IBX and BTI are recommended as the preferred reagents for regio-controlled oxidation of PAPs to PAQs.

Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds

Photoinduced electron-transfer reactions of several ketone substrates were studied to evaluate the utilities of 1,6-bis(dimethylamino)pyrene (BDMAP), 1,6-dimethoxypyrene (DMP), 9,10-bis(dimethylamino)anthracene (BDMAA), and 9,10-dimethoxyanthracene (DMA) as electron-donating sensitizers cooperating with 2-aryl-1,3-dimethylbenzimidazolines. BDMAP and DMP generally led higher conversion of ketones and better yield of reduction products compared to BDMAA and DMA.